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Coumarins

The coumarins are derived from the skeleton of coumarin. Within the coumarins coumarin plays the most important role. The coumarins are dicyclic and consist of a benzene ring and a lactone. In alkaline solution, the ester is cleaved, and the open-chain coumarin is water-soluble. Coumarins have, depending on the substitution, different solubility properties.

Coumarins have a wide physiological effects that make them interesting for medical applications.

Occurrence

Coumarins are found in various plants. For its high coumarin content especially the sweet clover (Melilotus L.), the woodruff (Galium odoratum L.) and the tonka bean (Dipteryx odorata [Aubl.] Willd.) are known. Many meadow plants, such as yarrow (Achillea millefolium L.) or angelica (Angelica archangelica L.) contain coumarins.

Coumarin derivatives

Coumarins

There are several coumarin derivatives, which are produced either directly from the plant, produced during the fermentation or be metabolized to these or made synthetically.

Furanocoumarins

Furanocoumarins occur naturally in several plants for example in hogweed but also in citrus plants. They are photoactive. They can damage the DNA by the linking of thymidine and cytosine by a [2+2] cycloaddition. Wherein the DNA is unusable, and the risk of cancer formation is thus increased. When applied to the skin it can cause rash and burns after sun exposure. In addition, however, psoriasis can be treated with proper dosage.

In the plant furanocoumarins are formed during infection. Furanocoumarins are antimicrobial and are thus able repel microorganisms.

4-Hydroxycoumarins

4-Hydroxycoumarins have a pharmacological effect on the human body. Dicumarol is formed in spoiled sweet clover (see fermentation) and leads to several coumarin-based drugs. The discovery of the effect of the anticoagulant dicoumarol led to the development of medical products such as warfarin. Warfarin is a drug derived from dicumarol which carries a skeleton of 4-hydroxycoumarin. Warfarin is prescribed today, mainly in the United States. Due to the difficult medication and the side effects it is shunned in Europe.

coumarins.txt ยท Last modified: 10.12.2014 by naturalproductswiki